11 Money-Saving Tricks for Booking Vacations on Kayak.com

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Chances are, you've used the popular travel search engine KAYAK to book a trip (or 85). First launched in 2004, the company now processes 1.5 billion searches a year and operates more than 40 international sites in 20 languages. And sure, you could make like a 23-year-old planning his first stint to Vegas and leave your vacation to the whim of crafty software calculations. Or, instead, use these tricks to get more out of your vacation, save money, and stay more organized along the way. 

1. Use the "freebies" filter when booking a hotel.
First, useful filters like neighborhood, location, and review scores can all be helpful in your hotel search. To make your search even handier though, after typing in your search results pop up, look for the "freebies" filter on the left rail. There, you can select options like free Internet, cancellation, breakfast, parking, and airport shuttle to zoom in on assets that are important for your trip.

2. Wait until the last minute.
Anniversary flowers, taxes, grocery shopping before a dinner party… we all know that waiting until the bitter end isn't always our best bet. But recent analysis of KAYAK's data shows that waiting until the very last minute (i.e. the day you want the room booked) can sometimes give you the best steals for hotel rooms. 

3. Sync Kayak with your Amazon Echo.
Besides the novelty of asking "Alexa, ask KAYAK where I can go for $500 dollars" being fun, adding the KAYAK skill to Alexa comes in handy for travel planning. The voice-activated travel search helps with flight tracking, plus checking prices on hotels, flights, and rental cars. (Learn more about this here.)

4. Or hit up Slack to book your travel.
If communicating via bot on the Slack messenger is more your speed (or you simply don't own an Echo), you can integrate the Kayak app for your booking convenience: "/kayak rental cars in New York City this Friday" or "/kayak direct flights from New York to Columbus," and you'll be on your way. Just wondering when one of your co-workers will land in Chicago for his sales meeting? Slack can tell you that, too. Note: To enable this app, you'll need to be a team admin on Slack or get approval from one of your colleagues who is.

5. Book your car at the right time.
You may be tempted to book a hotel, flights, and car rentals in one fell swoop, but sometimes strategically timing your purchases can pay off: A recent analysis of KAYAK's data revealed that you should book your car at least two weeks in advance for the best prices. For larger cities (think: New York, Chicago, L.A.), do it three weeks in advance to save the most money.

6. Spend less on flights with Kayak Explore.
Go here and search by price and flight time (check off the "nonstop only" box to search only for flights without connections) or routes to plan your next adventure. You'll be able to see all the available flights in a given time frame for up to about a year out while staying within your budget. A recent search for flights from Nashville for "Summer 2016 under $500" gave us choices ranging from Portland ($244) and Costa Rica ($338), to Boston ($137) and Anchorage ($469). You can also use Hacker Fares to keep more dough in your pocket on round-trip flights: These results in your flight searches combine multiple one-way flights to get you the best possible price.

7. Trust the "Price Forecast" tool.
Book today? Wait it out? You know flipping a coin won't help. And polling friends and family members will just lead to impasse. Instead, after entering your flight search, look to the left rail in your results screen to see a price trend report. The sophisticated algorithms used in the "Price Forecast" tool uses data from over a billion annual queries to anticipate whether airfares will rise or fall in the coming week.

8. Make group trip planning easier.
That shared Google doc of who's booked Park City flights and what time they're arriving isn't living up to your best-man duties in planning your buddy's bachelor party. Let everyone breathe a sigh of relief by using KAYAK's share function. After you book, select "Share this trip…" and you can also configure things so friends, family, and co-workers can edit the trip, instead of just viewing it. Always want your assistant or spouse in the loop for your travel? Go to your "Trips Settings" page here and enter their email address to the "Share new trips with…" section (again, you can also decide if you want to give them just viewing or editing access).

9. Select "Show flexible dates" when searching for flights.
You may know that mid-week travel during the summer is a no-brainer way to snag a deal. But a simple way to find better deals is making use of KAYAK's flexible dates options. After you click the drop-down arrow to "show flexible dates," you'll be presented with a "+/- 3 days" menu where you can select flight days from one to three days before/after what you've input (with options to select "use exact date" if you need to depart/return on a certain day). Easily compare value for the various available flights and book from there.

10. Book a vacation package.
Save clicks and cash: KAYAK found savings of up to 32 percent by choosing a flight and hotel package versus booking your flights and hotel separately. Savings vary throughout the year and where you want to go, but it's worth a quick perusal of their "Vacation Packages" tab to see if it makes sense for you.

11. Set Price Alerts to find the best deal.
Still owe your college roommate in Kansas City a visit (since 1999)? Use "Price Alerts" on your account, which does the grunt work for you and searches while you’re offline based on your criteria. As soon as hotel rates or airfares change, they'll send you a text or email.